06 May 2025 A Key Trait for Financial Success

Last week, I was listening to a podcast featuring one of my favorite financial writers, Morgan Housel, when he shared a moment that stuck with me. He recalled asking Daniel Kahneman—the renowned psychologist and co-recipient of the Nobel Prize in Economics—what trait matters most for achieving long-term financial success.

Kahneman’s answer?

“A well-calibrated sense of future regret.”

In other words, to make wise decisions with our money (and time) over the years, we need the ability to anticipate what we’re likely to regret down the road.

That idea stood out to me because, lately, I’ve been doing just that—quietly reflecting on the things I might one day regret. Not in a doom-and-gloom way, but as a practical framework to help ensure I’m using my time and money in ways that feel meaningful now and that I’ll feel good about later in life.

The reality is, if we’re not careful, it’s easy to let either today’s concerns or tomorrow’s plans become the exclusive drivers of our decisions. When that happens, the consequences can be significant. For some, it might mean working too hard and missing meaningful experiences with loved ones. For others, it could mean saving too little and entering retirement feeling stressed and unprepared. Maybe we’ll wish we had taken better care of our health—mentally, physically, or spiritually. Perhaps we’ll look back and regret how much time we spent worrying about things that never happened. Or maybe we’ll wish we had traveled more, deepened friendships, or said “yes” to things that brought us joy and perspective.

That’s why it’s so important to step back and consider how today’s choices might feel in hindsight.. The challenge is, we humans aren’t especially good at predicting what will make us happy—or what we’ll regret—later in life. On top of that, what we find important can shift as we grow, mature, and move through different seasons. That’s why this idea of considering future regret isn’t a one-time evaluation; it’s a process we need to revisit over time.

Going through this process myself has prompted a few small changes—not dramatic overhauls, just thoughtful shifts that better reflect what I believe will matter to me in 10 or 20 years. Some of my biggest takeaways have been:

• If we’re not intentional with how we spend our time and money, there’s a good chance our future selves will wish we had done things differently.
• It’s wise to revisit our list of potential regrets from time to time and recalibrate. Life changes. We change. Our priorities and goals change too.
• There’s no guaranteed way to avoid all future regrets, but one thing is clear: extremes tend to carry risk. Whether it’s saving every penny for a future that may never arrive or spending freely without a plan, both approaches can leave us vulnerable. A more balanced path—one that allows for flexibility, regular reflection, and thoughtful adjustments—offers a wiser, more sustainable way forward.
• Some of the louder voices in personal finance—whether they’re promoting FIRE (Financial Independence, Retire Early), YOLO (You Only Live Once), or the tried-and-true “save early and often”—can sometimes oversimplify complex trade-offs. While there’s wisdom in these broad principles, the real challenge lies in thoughtfully applying them to your own life, values, and goals.

If you’d like to explore what this might look like in your own life or financial plan, let us know. At Beacon, we’re always up for the conversation.